(6aR,6bS,8aS,13aS,13bR)-10-hydroxy-6a,8a-dimethyl-4-oxo-12-(thiophen-2-yl)-1,2,4,5,6,6a,6b,7,8,8a,12,13,13a,13b-tetradecahydronaphtho[2',1':4,5]indeno[1,2-b]pyran-11-carbonitrile | 1616254-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (6aR,6bS,8aS,13aS,13bR)-10-hydroxy-6a,8a-dimethyl-4-oxo-12-(thiophen-2-yl)-1,2,4,5,6,6a,6b,7,8,8a,12,13,13a,13b-tetradecahydronaphtho[2',1':4,5]indeno[1,2-b]pyran-11-carbonitrile
• 英文别名: (1R,2S,10S,13S,14R)-7-hydroxy-10,14-dimethyl-17-oxo-5-thiophen-2-yl-8-oxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-4(9),6,18-triene-6-carbonitrile
• CAS: 1616254-78-4
• 化学式: C₂₇H₂₉NO₃S
• 分子量: 447.598
• InChiKey: YFGYINHWRDIGTE-PJWRZIKHSA-N

物化性质

• 沸点：
  638.8±55.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  98.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 雄烯二酮 、 氰乙酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (6aR,6bS,8aS,13aS,13bR)-10-hydroxy-6a,8a-dimethyl-4-oxo-12-(thiophen-2-yl)-1,2,4,5,6,6a,6b,7,8,8a,12,13,13a,13b-tetradecahydronaphtho[2',1':4,5]indeno[1,2-b]pyran-11-carbonitrile
  参考文献：
  名称：

  Heterocyclic ring extension of androstenedione: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

  摘要：

  The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.04.011